Hydrochloric Acid → 2-((Phenylmethyl)thio)acetic acid

HRID 477305Notes

Reaction equation

HRID 477305 reaction equation
[OH-].[Na+].Br[CH2:4][C:5]([OH:7])=[O:6].[C:8]1([CH2:14][SH:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>O1CCCC1.ClCCl>[CH2:14]([S:15][CH2:4][C:5]([OH:7])=[O:6])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6227Bromoacetic AcidHCID 7509Benzyl mercaptanHCID 14798Sodium Hydroxide2×

Product 1

HCID 668972-((Phenylmethyl)thio)acetic acidYield 55.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

1N aqueous sodium hydroxide solution (500 cc), cooled to a temperature of approximately 5° C., is added in the course of 1 hour to bromoacetic acid (70 g). The mixture obtained is added to a solution of phenylmethanethiol (50 g) and 1N aqueous sodium hydroxide solution (500 cc) in tetrahydrofuran (500 cc), and then heated to approximately 100° C. for 90 minutes. The mixture is cooled to a temperature in the region of 5° C. There are added 12N aqueous hydrochloric acid solution (100 cc) and then dichloromethane (3,000 cc) in the course of 30 minutes. The organic phase is separated off after settling has taken place, and the aqueous phase is extracted with dichloromethane (2×200 cc). The organic phases are combined, dried over anhydrous magnesium sulphate, filtered and evaporated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residue is recrystallized in boiling cyclohexane (50 cc). (Benzylthio)acetic acid (40.5 g), m.p. 58°-60° C., is obtained.

Workup

  1. customThe mixture obtained
  2. temperatureThe mixture is cooled to a temperature in the region of 5° C
  3. customin the course of 30 minutes
  4. customThe organic phase is separated off after settling
  5. extractionthe aqueous phase is extracted with dichloromethane (2×200 cc)
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customevaporated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa)
  9. customThe residue is recrystallized

Sources & evidence

ORD record
ord-2b97e7c9e915432ead4897039e37a329
Source dataset
uspto-grants-1989_12
Patent number
US04886835

Reaction notes

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